Dichloromethane → HCID 67052403, compound

HRID 2426347Notes

Reaction equation

HRID 2426347 reaction equation
[CH3:1][CH:2]([CH3:16])[CH2:3][NH:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]=[CH:7][C:6]=1[NH2:15].ClCCl.C(N(CC)CC)C.[Cl:27][CH2:28][C:29](Cl)=O>ClCCCl>[Cl:27][CH2:28][C:29]1[N:4]([CH2:3][CH:2]([CH3:16])[CH3:1])[C:5]2[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[N:8]=[CH:7][C:6]=2[N:15]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 11298872N4-(2-methylpropyl)quinoline-3,4-diamine

Product 1

HCID 67052403HCID 67052403, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

N4-(2-Methylpropyl)quinoline-3,4-diamine (U.S. Pat. No. 5,389,640 Example 1, 41 g, 0.190 mol), dichloromethane (550 mL), triethylamine (40 mL, 0.286 mol), and chloroacetyl chloride (16.7 mL, 0.210 mol) were combined and then stirred at ambient temperature over the weekend. The reaction mixture was diluted with 1,2-dichloroethane (75 mL) and then washed with saturated aqueous sodium bicarbonate (3×400 mL). The organic layer was dried over magnesium sulfate, filtered through a layer of CELITE filter aid, and then concentrated under reduced pressure to provide 52.81 g of 2-chloromethyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline as a brown solid.

Workup

  1. washwashed with saturated aqueous sodium bicarbonate (3×400 mL)
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered through a layer of CELITE
  4. filtrationfilter aid
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e26ad77cb3024adc89e4d3d5eb1f154c
Source dataset
uspto-grants-2011_06
Patent number
US07968563B2

Reaction notes

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